(-)-Xestosaprol N 和 O 的全合成。

Total Synthesis of (-)-Xestosaprol N and O.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.

Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.

出版信息

Org Lett. 2018 Feb 2;20(3):732-735. doi: 10.1021/acs.orglett.7b03865. Epub 2018 Jan 19.

DOI:10.1021/acs.orglett.7b03865

PMID:29350045

Abstract

The first total synthesis of (-)-xestosaprol N and O is described. This synthetic work features a convergent strategy: (1) a Pd-catalyzed arylation followed by cyclization to build a naphthalene fragment (ring C, D); (2) utilization of (-)-quinic acid to construct the chiral hydroxyl group at C-2; (3) a substrate controlled intramolecular Heck reaction to construct a quaternary carbon center (ring B); (4) introduction of a hypotaurine moiety at a late stage to furnish the E ring.

摘要

首次全合成 (-)-xestosaprol N 和 O。该合成工作采用了一种收敛策略：(1) Pd 催化芳基化反应，然后环化构建萘环片段 (C、D 环)；(2) 利用 (-)-奎尼酸构建 C-2 位手性羟基；(3) 底物控制的分子内 Heck 反应构建季碳中心 (B 环)；(4) 在后期引入 hypotaurine 片段构建 E 环。